On his superb “Revisionist History” podcast the other day, Malcolm Gladwell made a passing mention of the 1920s tennis star Bill Tilden. The 1920s was probably the first golden age of American sports, and Tilden was a big part of that. Baseball had Babe Ruth. Boxing had Jack Dempsey. Golf had Bobby Jones. And tennis had Tilden.

Tilden was all but impossible to beat. From 1920 to 1926, just after he worked to make his backhand into a weapon, he won every single significant tournament he played in. Tilden was such a dominant force that in five-set matches he would sometimes purposely lose the first two sets and then lose four or five games in the second set before coming back to win. He was so much better than everyone else he simply needed to create challenges for himself.

Malcolm called him “arguably the greatest tennis player ever after Roger Federer.”

One of the repeating questions of this Greatest Ever Series — where we are not looking to name...